SML0406

Roquefortine C

≥98% (HPLC), (Penicillium crustosum)

• Synonym(s): 2H-Pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-5-ylmethylene)-,(3E,5aS,10bR,11aS)-, Roquefortine from Penicillium crustosum
• Empirical Formula (Hill Notation): C₂₂H₂₃N₅O₂
• CAS Number: 58735-64-1
• Molecular Weight: 389.45
• UNSPSC Code: 12161501
• NACRES: NA.77
• Assay: ≥98% (HPLC)

Properties

• Quality Segment: 200
• biological source: (Penicillium crustosum)
• assay: ≥98% (HPLC)
• solubility: chloroform: 1 mg/mL, ethyl acetate: 1 mg/mL, DMSO: 10 mg/mL, methanol: 10 mg/mL
• storage temp.: −20°C
• SMILES string: N21C3Nc4c(cccc4)C3(CC2C(=O)N\C(=C/c5nc[nH]c5)\C1=O)C(C)(C)C=C
• InChI: 1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9-
• InChI key: SPWSUFUPTSJWNG-SXGWCWSVSA-N

Description

Application

Roquefortine C has been used as a standard for the quantification of roquefortine C by high-performance liquid chromatography (HPLC). It has also been used as a standard for the quantification of roquefortine C by liquid chromatography-mass spectrometry (LC−MS/MS).[1]

Biochem/physiol Actions

Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species.

Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species. It has been found in blue cheese and in many other food products due to natural occurrence and contamination. Roquefortine C was found to be active on a wide range of organisms. It inhibits the growth of Gram-positive bacteria, and cockerels treated with roquefortine lost their righting reflex and died within 8-12 hours. Mice injected with roquefortine C experienced neurotoxic properties. Roquefortine C was also reported to inhibit cytochrome P450 as well as tubulin polymerization.

Preparation Note

Soluble in methanol (10 mg/mL), DMSO (10 mg/mL), ethyl acetate (1 mg/mL) and chloroform (1 mg/mL). DMSO solution at 10 mg/mL is stable for 3 months at −20 °C.

Safety Information

• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H373
• pcodes: P260 - P264 - P301 + P310 - P314 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - STOT RE 2
• target_organs: Nervous system
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects